The 25 Most Embarrassing Moments in MLB History

The 25 Most Embarrassing Moments in MLB History

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Professional sports are littered with moments in time where players have been subjected to less than stellar incidents that they would no doubt love to take back. While they are still professionals, they are still human beings, and as a result have been a party to specific plays that were embarrassing in nature.

MLB players are certainly no exception, and throughout the course of baseball history there have been plays and events which have been documented and played over and over again ad nauseum, much to the chagrin of the players involved.

While we remember all of the greatest plays ever recorded, we also remember all of the embarrassing ones as well, and oftentimes get more joy and satisfaction when watching the foibles of others.

Here then is our list of the 25 most embarrassing moments in MLB history.

Doug Mead is a featured columnist with Bleacher Report. His work has been featured on the Seattle Post-Intelligencer, SF Gate, CBS Sports, the Los Angeles Times and the Houston Chronicle. Follow Doug on Twitter, @Sports_A_Holic.

Honorable Mention: Bill Buckner, 1986 World Series, Game 6

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Poor Bill Buckner. The guy never seems to get a break from making lists such as this one. However, this time we’ll give him a little bit of a break.

While his egregious error in Game 6 of the 1986 World Series that allowed Ray Knight to score the winning is certainly one of the most watched errors in major league history, it was also quite embarrassing for Buckner, who forever has to endure the ignominy of the play over and over again.

25. Babe Ruth Sold by Boston Red Sox

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In 1919, Boston Red Sox owner Harry Frazee made a transaction that forever tarnished his name and saddled the Red Sox with a supposed curse that would not be lifted until 2004.

In late December of that year, Frazee sold Red Sox star pitcher Babe Ruth to the New York Yankees for $125,000 plus a $300,000 loan for the mortgage on Fenway Park. While many reports at the time pointed to Frazee using the money to finance his play No, No, Nanette, those reports have since been disputed and debunked.

Whatever the reason, Frazee’s transaction turned him into an instant pariah and sparked the Curse of the Bambino, which was finally put to rest with the Red Sox World Series victory in 2004.

On Dec. 9, 1965, Cincinnati Reds GM Bill DeWitt made a decision that will forever be looked at as one of the worst trades in the history of baseball, and certainly one that was embarrassing in nature.

DeWitt made the claim that his right fielder, Frank Robinson, was “an old 30,” and decided to trade him to the Baltimore Orioles for pitchers Milt Pappas and Jack Baldschun and outfielder Dick Simpson.

All Robinson did in his first season with the Orioles as “an old 30” player was to win the American League Triple Crown, the AL MVP award and led the Orioles to their first-ever World Series championship, winning the MVP of that series as well.

In Robinson’s six seasons with the Orioles, he would help lead them to the World Series four times, again winning the championship in 1970.

23. St. Louis Cardinals Owner Gussie Busch Trades Steve Carlton

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In February of 1972, southpaw Steve Carlton, who had posted his first 20-win season of his career the year before with the St. Louis Cardinals, was embroiled in a contract dispute with then-owner Gussie Busch. The two sides were only $10,000 apart, but neither side was willing to budge.

Busch had taken the stance that he was going to follow the directive of then-President Richard Nixon, who had ordered wage and price controls for the country at that time. Since Carlton was unwilling to back down from his demands, Busch called Carlton “unpatriotic,” and ordered his general manager, Bing Devine to immediately trade Carlton.

On Feb. 25, 1972, Carlton was traded to the Philadelphia Phillies for pitcher Rick Wise. While Wise was an excellent pitcher at the time, he only lasted two years in St. Louis. Meanwhile, Carlton put together one of the most incredible seasons for any pitcher in history, leading the league in wins (27), complete games (30), ERA (1.97), strikeouts (310) and innings pitched (346.1).

Carlton went on to win the first of his four Cy Young awards that year, and the trade has been hailed as one of the worst and most lopsided in baseball history.

22. Willie Davis: Game 2, 1966 World Series

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By all accounts, Los Angeles Dodgers center fielder Willie Davis was considered a very reliable outfielder, and he would go on to win three Gold Glove awards during his career. However on Oct. 6, 1966 at Dodger Stadium in Los Angeles, Davis had an inning that can only make one want to crawl into a hole and die.

The game between the Dodgers and the upstart Baltimore Orioles was tied heading into the top of the fifth inning, and the Dodgers had future Hall of Fame pitcher Sandy Koufax on the mound. After Boog Powell led off the inning with a single, Paul Blair hit a routine fly ball to Davis out in center. However, Davis completely lost the ball in the sun for an error, putting runners on first and second. The next batter, catcher Andy Etchebarren, also hit a fly ball to center. Davis first bobbled, and then dropped the ball. Powell scored from second on the play, and Blair rounded second and took off for third. Davis saw Blair running and launched a throw to third that was way over the head of third baseman Jim Gilliam, allowing Blair to score.

The Orioles would go on to score one more run off Koufax, and would win the game 6-0, on the way to sweeping the World Series.

21. Bob Tillman: May 12, 1967

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In early May 1967, the Boston Red Sox were taking on the Detroit Tigers in the first of a four-game series at Fenway Park. The Tigers had taken control of the game, scoring four runs off Sox starter Bucky Brandon, and by the time the eighth inning rolled around, Brandon was gone and replaced by reliever John Wyatt.

After retiring the first batter, Wyatt allowed a walk to Tigers slugger Al Kaline. Kaline then attempted to steal second base. Red Sox catcher Bob Tillman came up out of his crouch, threw the ball to second to try to nail Kaline, and instead nailed his own pitcher Wyatt in the head.

The ball caromed off to the on-deck circle, with Kaline taking third on the play. Wyatt wobbled around for a bit, but amazingly stayed in the game and came back to pitch a 1-2-3 ninth inning.

Tillman was not in the lineup the following day.

20. Babe Ruth: Game 7, 1926 World Series

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The 1926 World Series featured the favored New York Yankees over the St. Louis Cardinals, who were playing in their first-ever Fall Classic. In spite of their favored status, the Yankees found themselves tied with the Cards after six games.

Game 7 was a tight affair, as the Cardinals rode a three-run fourth inning and a one-run lead into the bottom of the ninth inning. After Cardinals reliever Pete Alexander retired the first two batters in the ninth, Alexander walked Babe Ruth. With Ruth on first and two out, Bob Meusel strode to the plate for the Bronx Bombers, representing the winning run.

However, Ruth decided to try and put himself into scoring position by attempting to steal second base. Ruth was thrown out by Cardinals catcher Bob O’Farrell, and the Cardinals had their first ever World Series championship.

It remains the only World Series ever to have ended on a caught stealing.

19. Leon Durham: Game 5, 1984 NLCS

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The 1984 National League Championship Series featured the Chicago Cubs, who hadn’t been to the postseason since 1945, and the San Diego Padres, who had never been to the playoffs since their inception in 1969. The series was tied 2-2, and Game 5 would determine who would go on and who would go home.

The Cubs got off the ground quickly, jumping out to a 3-0 lead. The Padres scratched their way back in the sixth via two sacrifice flies to cut the Cubs lead to one. In the bottom of the seventh, Carmelo Martinez led off the inning with a walk and was sacrificed to second by shortstop Garry Templeton.

The next batter, Tim Flannery, then hit a routine grounder to first base. Cubs first baseman Leon Durham let the ball trickle through his legs, scoring Templeton and tying the game at 3-3. The Cubs completely unraveled after that, allowing another three runs and losing the game and the NLCS.

Durham’s error became another in many storied collapses in Cubs history.

18. Tim McCarver: July 4, 1976

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On July 4, 1976, the United States was celebrating its bicentennial, and the Philadelphia Phillies were on their way to their first 100-win season in franchise history. Catcher Tim McCarver at that point in time had more or less become the personal catcher for Steve Carlton, and was in the waning years of his career.

However, on July 4, 1976, McCarver had what was definitely not a shining moment in his career. In the first game of a doubleheader against the Pittsburgh Pirates, the Phillies put together a rally in the top of the second inning. With the bases loaded, McCarver came up to face Larry Demery.

McCarver launched a deep fly ball that cleared the fence for a grand-slam home run. However, McCarver was running just a wee bit too fast, and passed teammate Garry Maddox, who was between first and second base, waiting to see if the ball had cleared the fence.

The umpire called McCarver out and awarded him with a three-run single, and McCarver’s blunder was honored in The Baseball Hall of SHAME 3 book.

17. Mike Grady: New York Giants, 1895

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In 1895 while playing for the New York Giants, third baseman Mike Grady made history that still stands as a record today.

On on particular play, a ground ball was hit Grady’s way. Grady bobbled the ball, enabling the runner to reach first. Grady threw the ball anyway, and the ball sailed wide of the bag for Grady’s second error. However, he wasn’t done. The Giants’ right fielder retrieved the errant throw, saw the runner rounding second, and threw the ball to Grady at third. Grady dropped the throw, with the ball rolling away toward left field. Grady retrieved the ball and attempted to throw the runner out at home. However, Grady threw the ball over the catcher’s head, officially giving Grady four errors on the same play!

16. Fred Merkle: New York Giants, 1908

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Fred Merkle ended up having a long career in baseball, playing 20 seasons for four teams. However in 1908, Merkle made one boneheaded move that forever defined his career.

On Sept. 23, 1908, Merkle was the first baseman for the New York Giants, and the Giants were playing the Chicago Cubs. The two teams were at the top of the National League and were fighting for the pennant.

Merkle came to the plate with the scored tied 1-1 in the bottom of the ninth. With Moose McCormick on first base, Merkle singled McCormick to third. The next batter, Al Bidwell, followed with another single, scoring McCormick with the winning run.

Giants fans raced onto the field to celebrate the win, and Merkle, without touching second base, trotted back to the dugout. Cubs second baseman Johnny Evers noticed Merkle had not touched second base, retrieved the ball from the outfield, and touched second, appealing to umpire Hank O’Day who ruled Merkle out on the play. Since Merkle did not touch second, McCormick’s run was disallowed, returning the game to a tie.

The game would be suspended because the fans would not clear the field, and back then, suspended games were played all over again. The Giants and Cubs made up the suspended game at the end of the season with the Cubs winning and moving on to the World Series.

Merkle’s embarrassing moment would forever be called Merkle’s Boner.

15. Robin Ventura: Chicago White Sox, 1993

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In 1993, third baseman Robin Ventura was a budding young player for the Chicago White Sox. On one particular day, Ventura made a decision that turned his name into mud in the state of Texas.

In 1993, Ryan’s 26th and last season in the major leagues, while pitching for the Texas Rangers, Ryan drilled Ventura with a pitch in the ribs. Ventura made the ill-advised decision to charge the mound and challenge the 46-year-old pitching legend. Ryan comported himself better than well, locking Ventura in a headlock and landing at least six head shots against the player 20 years his junior.

To this day, the video of the incident is still played in Rangers Ballpark in Arlington from time to time, much to the delight of the frenzied faithful Ryan fans.

14. Mickey Owen: Game 4, 1941 World Series

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During the first four years of Mickey Owen’s career, he was considered an excellent defensive catcher, and in his first year with the Brooklyn Dodgers in 1941, Owen set a record for most errorless fielding chances by a catcher with 508 perfect attempts. But later that year, Owen made a gaffe that made the top of the list among embarrassing plays in MLB history.

With the Dodgers trailing in the World Series two games to one to the favored New York Yankees, the Dodgers held a 4-3 lead in the top of ninth inning. With two outs, Yankees hitter Tommy Henrich swung and missed at strike three, tying the series at two games apiece.

But wait! Owen, is unable to hang onto strike three, and the ball bounds back toward toward the first base dugout. Henrich reaches first base safely, and the Dodgers, clearly rattled, allowed the Yankees to rally and score four runs to take Game 4, 7-4. The following day, the Yankees captured Game 5 to win the 1941 World Series.

13. Tommy John: July 27, 1988

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Tommy John may be remembered for his long career and the renowned surgery that bears his name, but he is also known for tying an inglorious modern-day record.

On July 27, 1988, while pitching for the New York Yankees, in a game against the Milwaukee Brewers, John had a ball hit back to him in the box. John muffed the grounder for the first error, then threw the ball wildly past first base for the second. Yankees right fielder Dave Winfield, retrieved the errant throw and attempted to throw the runner out at home, inexplicably, John intercepted the throw and then threw wildly past the catcher for his third error on the play.

Famous for Tommy John surgery? Yes. Also famous for embarrassment on the ballfield? Yes.

12. Milton Bradley: Chicago Cubs, June 12, 2009

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Outfielder Milton Bradley has certainly been involved in more than his share of exploits on the ballfield, most of them involving his famous temper. However on June 12, 2009, Bradley became known for embarrassment on the field of play as well.

In an interleague game against the Minnesota Twins, in the top of the eighth inning with runners on first and third with one out, Twins catcher Joe Mauer hit a deep fly ball to Bradley in right field. Bradley caught the ball, and thinking it was the third out of the inning, flipped the ball into the stands and started trotting back to the dugout.

Little did Bradley know that there was only one out at the time, and the runner on third, Nick Punto, was allowed to score on the play and Brendan Harris was awarded third base.

Bradley can be called a lot of things, but rocket scientist probably won’t be one of them.

11. Benny Agbayani: August 12, 2000

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Outfielder Benny Agbayani enjoyed a brief five-year career in the majors, but one play in 2000 pretty much defined his career.

On Aug. 12, in a game against the San Francisco Giants, during the fourth inning the Giants had loaded the bases against the New York Mets with just one out. Catcher Bobby Estalella lifted a high pop fly to Agbayani in left field. Agbayani made the catch and then flipped the ball to a youngster in the stands. Agbayani started trotting back to the dugout, and within a few seconds suddenly realized that there was just one out. Agbayani went back, retrieved the ball from the youngster and attempted to throw home.

However, the umpire ruled that since the ball had already left the field of play, all runners on base were awarded two bases, scoring two runners.

Fortunately, the Mets still won the game 3-2, and Agbayani later gave another ball to the young fan who he had previously and famously flipped the ball to.

10. Larry Walker: August 24, 1994

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In late August, in a game against the Los Angeles Dodgers, Montreal Expos right fielder Larry Walker ambled over to the right field foul line and made a catch in fair territory for what he thought was the third out of the inning. Walker gave the ball to a youngster in the stands.

However, once again, there was only one out! Walker ran back, grabbed the ball and threw it back to the infield. Again, the umpire ruled the ball had already left the field of play, and awarded Dodgers’ first baseman Jose Offerman third base on the play.

No one scored on the play, so no harm, no foul. However, the play still makes our list.

9. Eddie Joost: Sept. 11, 1948

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In the bottom of the fourth inning in a game against the Boston Red Sox, Philadelphia Athletics shortstop Eddie Joost pulled off a trick play that was definitely not planned and turned into one of the funniest moments in baseball history.

With Billy Goodman at the plate for the Red Sox and Ted Williams on second base, Goodman hit a grounder to short. Joost ran over to make the play, but somehow, the ball had bounced off the heel of his glove, rolled up his sleeve and ended up inside the back of his shirt!

Joost frantically tried to retrieve the ball, jumping up and down like he had been attacked by bees. When that didn’t loosen the ball, he finally ripped the shirttails out of his pants, and the ball dropped.

Meanwhile, Goodman reached first on the error. But Williams, who had raced to third base on the play, could have easily scored while Joost was doing his magic dance trying to retrieve the ball, but Williams was laughing so hard at the play he forgot to run home.

“I picked up the ball and ran over to third base,” Joost recalled. “I shook the ball in Ted’s face and yelled at him, ‘Okay, damn you! You can run now.’

“But he was laughing so hard he couldn’t have run if he wanted to. Everybody was laughing—even me.”

Source: The Baseball Hall of Shame 4 By Bruce Nash, Allan Zullo

8. Sammy Sosa: Chicago Cubs, June 3, 2003

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On Tuesday night, June 3, 2003 in game against the Tampa Bay Devil Rays, Chicago Cubs right fielder Sammy Sosa was at the plate in the first inning with runners on second and third.

Sosa then hit a grounder to second base, his bat shattering during the process. When the bat was picked up, the umpires found bits of cork inside the broken bat, and immediately ejected Sosa.

Sosa tried to explain things later after the game, saying that the bat was used "by mistake." Wink, wink.

"I use that bat for batting practice," Sosa said at the time. "It's something that I take the blame for. It's a mistake, I know that. I feel sorry. I just apologize to everybody that are embarrassed."

Um, Sammy--why would anyone else be embarrassed?

7. Nyjer Morgan: May 22, 2010

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On May 22, 2010, in an interleague game against the Baltimore Orioles, Washington Nationals center fielder Nyjer Morgan let his emotions get the best of him in a play that will be forever repeated on blooper videos for some time to come.

In the fourth inning, Orioles center Adam Jones was at the plate and lifted a high drive deep to center field. Morgan went back on the ball, and when he made contact with the wall was exactly when the ball landed in his glove. The incidental contact knocked the ball out of Morgan's glove.

While Morgan decided to throw a hissy fit about not catching the ball, Jones continued racing around the bases, and by the time the Nationals' left fielder retrieved the ball and threw it home, Jones had himself a nice, tidy inside-the-park home run.

6. Alex Rodriguez: Game 6, 2004 ALCS

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Poor Alex Rodriguez. He has endured criticism regarding money, contracts, agents, girlfriends, steroids and a number of other supposed actions. But on October 20, 2004, A-Rod endured the humility and embarrassment of a really stupid play.

In Game 6 of the 2004 ALCS against the Boston Red Sox, Rodriguez was called out for interference after attempting to swat the ball from the glove of pitcher Bronson Arroyo. Derek Jeter was ruled back to first base and the Yankee rally was effectively killed.

According to Section 6.1 of the MLB Umpire Manual, "While contact may occur between a fielder and runner during a tag attempt, a runner is not allowed to use his hands or arms to commit an obviously malicious or unsportsmanlike act."

5. Ryan Raburn: April 26, 2011

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On April 26, 2011, Detroit Tigers left fielder Ryan Raburn turned what should have been a Miguel Olivo flyout into an improbable home run.

There have been quite a few players in baseball history who have knocked the ball over the fence trying to catch a ball, but Raburn may just be the first one to it from the beginning of the warning track.

4. Manny Ramirez: July 21, 2004

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We could probably do a highlight reel alone based on Manny Ramirez embarrassing moments, but this particular one really takes the cake.

The incredible part about the play was that Manny probably made the best dive of his life on the throw.

3. Roger Clemens: Game 2, 2000 World Series

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In the infamous Subway Series of 2000 pitting the New York Yankees against the New York Mets, emotions were clearly at a high between Yankees pitcher Roger Clemens and Mets catcher Mike Piazza. To say that the two didn't like each other is akin to saying that the Red Sox and Yankees is just a rivalry between friends.

But in Game 2, Clemens re-sparked the hot feelings between each other when Piazza broke his bat on one swing, with the barrel of the bat headed towards the mound. Clemens' actions regarding throwing the bat toward Piazza will forever be questioned.

2. Steve Lyons: Aug. 13, 1990

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On August 13, 1990 Chicago White Sox utility player Steve Lyons, who was already known for being just a bit off-kilter at times, bunted down the first base line and just barely beat the throw to the bag on a head-first slide.

After getting up, Lyons decided to do a little bit more than just dust himself off. Lyons forever became for being the first ballplayer in history to drop his pants during a game.

Legend has it that women behind the Chicago White Sox dugout were throwing dollar bills at Lyons after he returned to the dugout at the end of the inning.

1. Jose Canseco: May 26, 1993

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Was there really any question that this particular play by Texas Rangers right fielder Jose Canseco wouldn't have been the all-time most embarrassing play in baseball?

Canseco was never known for being an outstanding defensive ballplayer, but no one ever thought he would use his head on ANY particular defensive play.